Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | HCID 23369640 | HCID 23369640 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 23369691 | HCID 23369691 | 98.6% |
Reaction Steps
2-(2-Hydroxyethyl)-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one (1.65 g) was suspended in dimethylformamide (20 ml). To the suspension, pyridine (20 ml) and methanesulfonyl chloride (1.5 ml) were added thereto, and the mixture was stirred for 6 hours. When the reaction was completed, methanol (20 ml) was added while cooling the mixture on ice, followed by mixing for 20 minutes. Subsequently, the reaction mixture was condensed under reduced pressure, to which water was added and extracted with chloroform. The chloroform phase was dried and condensed under reduced pressure. The resultant residue was recrystallized from a solvent mixture of chloroform-ether to obtain 1.75 of 2-(2-chloroethyl)-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one as pale yellow needles (98.6%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05576324 |
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| Source dataset | uspto-grants-1996_11 |
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| ORD ID | ord-5f9280c59c424bc9a6ca8352af9839f4 |
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| Source note | uspto-grants-1996_11 |
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